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Chemo‐, Regio‐, and Stereoselective Cyclizations of 1,3‐Bis(trimethylsilyloxy)‐1,3‐butadienes with α ‐Chloroacetic Acid Chlorides and α ‐Chloroacetic Acetals
Author(s) -
Langer Peter,
Krummel Thilo
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010417)7:8<1720::aid-chem17200>3.0.co;2-e
Subject(s) - regioselectivity , chemistry , chloroacetic acid , lewis acids and bases , stereoselectivity , acetal , stereochemistry , organic chemistry , catalysis
Treatment of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes with α ‐chlorocarboxylic acid chlorides resulted in chemo‐ and regioselective formation of 6‐chloro‐3,5‐dioxo esters, which were regioselectively converted into functionalised 3(2 H )furanones. Chemo‐ and regioselective condensation of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes with α ‐chloroacetic dimethyl acetal afforded 6‐chloro‐5‐methoxy‐3‐oxo esters, which could be regio‐ and stereoselectively transformed into 2‐alkylidene‐4‐methoxytetrahydrofurans.